Hariamide, a Novel Sulfated Sphingolipid from a <i>Zoanthus</i> sp. of the Indian Coast

Babu, Uddagiri Venkanna; Bhandari, S. P. S.; Garg, H. S.

doi:10.1021/np970267k

Cited by 13 publications

(9 citation statements)

References 5 publications

(6 reference statements)

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“…As the formula was C 34 H 69 NO 7 S, the structure of 1 was, assigned as N-[2-hydroxy-1-(hydroxymethyl)-3-(sulfooxy)heptadecyl]hexadecanamide, and named ircisulfamide. (6 ± 16) 29.3 ± 29.7 (t) 1.20 ± 1.34 ± CH 2 (17) 22.7 (t) ± ± Me (18) 14…”

Section: Results Andmentioning

confidence: 98%

“…Solvolysis [17] of 1 afforded the desulfated ceramide 1a, which has been reported before [15]. Its resonances at d(C) 62.0 (C(1)) 52.8 (C(2)), 76.7 (C(3)), and 72.3 (C(4)) were very similar to the ones reported (61.9, 52.7, 76.5, and 71.9, resp.)…”

Section: Results Andmentioning

confidence: 99%

“…By comparing the NMR chemical shifts of HÀC(2) and C(1) to C(3), C(1'), and C(2') with those of known glucosphingolipids [3] [21], the relative configuration of 2 was determined as (2S,3R,2'R) (6) 33.8 (t) 2.06 (m) H ÀC(5), HÀC(7) CH 2 (7) 35.4 (t) 2.04 (m) H ÀC(6), HÀC(8) HÀC (8) 124.8 (d) 5.14 (t, J 6.5) HÀC (7), HÀC(19) C (9) 136.6 (s) ± H ÀC(8), HÀC(10) CH 2 (10) 40.8 (t) 1.98 (t, J 7.5) ± CH 2 (11 ± 16) 30.4 ± 30.8 (t) 1.20 ± 1.35 ± CH 2 (17) 23.7 (t) 1.20 ± 1.35 ± Me (18) 14.5 (q) 0.90 (t, J 7.0) ± Me (19) 16.2 (q) Extraction and Isolation. The dried marine sponge (500 g) was extracted with 95% aq.…”

Section: Results Andmentioning

confidence: 99%

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Two New Ceramides from the Marine Sponge Ircinia fasciculata

Zhang

et al. 2005

Helvetica Chimica Acta

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A new 4-sulfated ceramide, ircisulfamide ( N-[(1S*,2S*,3R*)-2-hydroxy-1-(hydroxymethyl)-3-(sulfooxy)-heptadecyl]hexadecanamide; 1), and a new glycosphingolipid, ircicerebroside ( (2R*)-N-{(1S*,2R*,3E,7E)-1-[(b-d-glucopyranosyloxy)methyl]-2-hydroxy-8-methylheptadeca-3,7-dienyl}-2-hydroxyeicosanamide; 2), were isolated from the aqueous EtOH extract of the marine sponge Ircinia fasciculata (Pallas). The structures of the new compounds were elucidated on the basis of spectroscopic analysis and by means of chemical methods.Introduction. ± Different sphingolipids such as ceramide, sphingosine, and sphingosine-1-phosphate have been isolated from marine vertebrates, invertebrates, algae, and fungi etc. [1 ± 3]. These compounds have received increasing attention in the last years as some of their derivatives act as endogenous cell-function modulators and secondary messengers [4]. Sphingolipids have been shown to be potent and specific inhibitors of protein kinase C [5], Na-and K-ATPase, and calmodulin kinase, and to activate phospholipase C, phospholipase D, casein kinase II, tyrosine kinase, and DG kinase [6]. In addition, sphingolipids can also induce Ca 2 release [7], proliferate cells [8], protect human keratinocytes from apoptosis [9], suppress colon carcinogenesis in rats [10], and enhance apoptosis of radiation-resistant prostate cancer cells [11].In continuation of our search for potent bioactive secondary metabolites from the marine invertebrates [12 ± 14], a new 4-sulfated ceramide, ircisulfamide (1), and a new glycosphingolipid, ircicerebroside (2), were isolated from the aqueous EtOH extract of the marine sponge Ircinia fasciculata. The structures of compounds 1 and 2 were elucidated on the basis of spectroscopic analysis and chemical methods.

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Section: Results Andmentioning

confidence: 98%

Section: Results Andmentioning

confidence: 99%

Section: Results Andmentioning

confidence: 99%

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Two New Ceramides from the Marine Sponge Ircinia fasciculata

Zhang

et al. 2005

Helvetica Chimica Acta

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“…Hence, it was postulated that this extract may contain ceramide and was analysed by TLC using various derivatizing reagents, namely, resorcinol‐sulfuric acid; cupric acetate reagent; ninhydrin reagent; Dragendorff's reagent which, gave a characteristic color indicating nitrogen containing functional group. Based on the above observations, it was suggested that the said extract may contain ceramide compounds as reported in the rice bran (Babu, Bhandari, & Garg, ; Cremesti & Fischl, ; Dixit, Khan, Swarnkar, Chattopadhyay, & Maurya, ; Ishii, Okino, & Mino, ).…”

Section: Discussionmentioning

confidence: 87%

In vitro anti-inflammatory and skin protective properties of extract comprising ceramides from de-oiled rice bran

Sahoo¹,

Varma²,

Patel³

et al. 2017

Journal of Food Biochemistry

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De‐oiled rice bran is a byproduct of rice processing industries and rich in lipids, carbohydrates, proteins, and fibers. Although rich in nutrients, it is unfit for human consumption and used as animal feed. This study was conducted to explore the therapeutic value of rice bran ceramides. Methanolic extract of de‐oiled rice bran (RBE) was obtained by hot soxhlet extraction method and evaluated for presence of ceramide. Further, the rice bran ceramide extract (RBE) was subjected to column chromatography and the presence of ceramide ascertained by spectroscopic studies. Cytotoxic effect of RBE was tested on THP‐1 and HaCaT cells. The tested concentrations of RBE (100 and 200 µg/mL) dose‐dependently inhibited lipopolysaccharide induced pro‐inflammatory cytokines (TNF‐α, IFN‐γ, IL‐8, IL‐6, and IL‐5) in THP‐1 cells. RBE enhanced skin‐barrier function (involucrin and filaggrin) in HaCaT cells, up‐regulated aquaporin‐3 (AQP‐3) expression, and inhibited hyaluronidase activity in HaCaT cells. Thus, RBE exhibited significant anti‐inflammatory and skin protective benefits in vitro. Practical applications De‐oiled rice bran is cheap, easily procurable, rich in phytonutrients, and possess therapeutic value. In the current study, extract comprising ceramides from de‐oiled rice bran (RBE) showed significant anti‐inflammatory and skin protective effects on THP‐1 and HaCaT cells, respectively. The results of the present investigation highlights the promising use of rice bran ceramides as potential anti‐inflammatory and skin protective ingredient in nutritional and skin‐care formulations or products.

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“…Zoanthamine was first isolated from zoantharians along the coast of Vishkapatanam by Rao et al (1984). Later, a novel sulfated sphingolipid (Hariamide) and 2-deoxyecdysterone (a novel oxytoxic agent) were extracted by Babu et al (1997) and Parameswaran et al (2001) from Zoanthus sp.Green Fluorescent Proteins (GFP) were extracted from Z. sansibaricus by Mythili and Gophane 2013. Studies describing the occurrence of zoantharian along the coast of the Indian subcontinent were carried out by Hornell (1910), Bhattiji (2010), Kaladhran et al (2011), Pandya et al (2013 and Trivedi et al (2014).…”

Section: Notes On Geographic Distributionmentioning

confidence: 99%

First record of Zoanthus gigantus Reimer & Tsukahara, 2006 (Anthozoa, Hexacorallia) from Indian waters, South Asia

Kumari¹,

Zacharia²,

Sreenath³

et al. 2017

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Zoanthus gigantus, family Zoanthidae, is reported for the first time from south Asia. The earlier distribution of the species has been known only from Japan, China, and Taiwan waters. Colonies of Z. gigantus were noticed along Saurashtra coast, Gujarat, during a field survey, in frame of monitoring Zoantharian diversity along Indian coast. Species was identified using morphological and histological examination. The occurrence of Z. gigantus from this additional biogeographic region highlights the distribution range extension of the species.

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Hariamide, a Novel Sulfated Sphingolipid from a Zoanthus sp. of the Indian Coast

Cited by 13 publications

References 5 publications

Two New Ceramides from the Marine Sponge Ircinia fasciculata

Two New Ceramides from the Marine Sponge Ircinia fasciculata

In vitro anti-inflammatory and skin protective properties of extract comprising ceramides from de-oiled rice bran

First record of Zoanthus gigantus Reimer & Tsukahara, 2006 (Anthozoa, Hexacorallia) from Indian waters, South Asia

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Hariamide, a Novel Sulfated Sphingolipid from a Zoanthus sp. of the Indian Coast

Cited by 13 publications

References 5 publications

Two New Ceramides from the Marine Sponge Ircinia fasciculata

Two New Ceramides from the Marine Sponge Ircinia fasciculata

In vitro anti-inflammatory and skin protective properties of extract comprising ceramides from de-oiled rice bran

First record of Zoanthus gigantus Reimer &amp; Tsukahara, 2006&nbsp;(Anthozoa, Hexacorallia) from Indian waters, South Asia

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First record of Zoanthus gigantus Reimer & Tsukahara, 2006 (Anthozoa, Hexacorallia) from Indian waters, South Asia